Note: This story was dynamically reformatted for online reading convenience. This is my true journey into sex with other men. It was bound to happen eventually, the only real question was who and when. What was "it"? Sex with another man...full on, cock sucking, ass fucking sex with another man. But let me explain why it was bound to happen first. Having been in a loveless marriage for far too many years, I, like a lot of men, took matters into my own hands. Of course, masturbation in my separate bedroom was a daily thing. I don't even remember how it started, but eventually, I found that I really, really enjoyed playing with my own ass while slowly playing with my hard cock. It became an obsession actually. One thing led to another, and I found myself at the local adult store, looking at sex toys. By my reasoning, if my finger felt that good, how would something bigger and longer feel? Of course, the choices were overwhelming, and the first time I went shopping, my brain went into overload. How the hell could someone get some of those toys in them? The selection went from minuscule to oh my fucking god. So, with some shame and trepidation, I finally selected something about the same size as my own cock. I'm not big by any stretch of the imagination, just a normal guy with a normal cock. A good 6 and a half inches, not too wide, but the little guy makes me happy, so I'm good with it. I was scared shitless that first time. Would anyone know why I was buying a fake cock? Would they look at me and wonder what kind of sick fuck would be buying a dildo? It took a few minutes to screw up my courage and walk to the front of the store with my selection, something a bit bigger than my own cock, but I finally swallowed hard and made my way to the front. Placing the rubber cock on the counter, the guy acted like he had seen it thousands of times before (of course, he had), and rang up my new best friend. Of course, the then pushed me further into humiliation, and asked if I wanted any lube to go with it. I didn't know whether to run out in embarrassment or slap myself for not thinking of it myself, so of course I lied and said no, I have plenty at home. Paying, I got out of there as fast as I could, and stopped at the drug store on the way home to buy lube that I said I already had and a fleet enema kit. Finally, at home, I raced to my room, excited as a little school girl. Going to the bathroom, I knew I needed to clean myself out a little bit first, so grabbed the kit and took care of that little issue first. Now there was a different experience! Who would have known that there would be cramping and a little pain to go with that part of this, but I got through it, all the while thinking of what was to come. Finally, I got to the bed to give the toy a try, and unknown to me at the time, enter a new chapter of my life. Squeezing a bunch of lube out, I got the toy all slick and shiny, and then used what was left on my hand to get my ass lubed up. By the time I was done with that, my cock was painfully hard in anticipation of what was to come. Not knowing enough at the time, I put the fake cock at my ass, and started to push it in. It took less than a minute for me to almost scream fuck as the thing popped in my ass. Damn, it hurt! What the hell was I thinking? My ass ring was pulsing and twitching from the pain of that monster sliding in. My own cock had retreated in surrender. I would later learn that a little prep work would be in order, but since I didn't know it at the time, I was laying there with my ass painfully twitching around this monster cock. Just as I was about to pull it out, the pain started getting less and less, and I started noticing the feeling of being open and stretched. It wasn't unpleasant, so I decided to leave it in and see where it went. Finally, after a bit of time, the pain was finally gone, and I pushed it in a little further. I started feeling more and more full. It was a good feeling, but different than anything I had ever experienced. Soon, I was in far enough that I bumped into my prostate, and my world changed! Fucking hell, that felt good. I stopped the forward movement and laid there enjoying that new and exciting feeling. Accidentally bumping the dildo in my ass, I felt those new and exciting feeling multiply, so I began slowly and carefully inching the dildo back and forth on that wonderful spot. It was heaven, and I got lost in that feeling for a while. My own little man was coming back to life, so I started massaging him with one hand as I delicately moved my new best friend back and forth over that spot that felt so good. After a few minutes, or an hour, I don't really know, I finally started pushing that dildo in a little further. Eventually, I came the second obstacle, who the hell would have known there was a second sphincter in there? Regardless, I kept steady pressure on it, and it eventually gave way. The dildo, after concurring that, slid the rest of the way in quickly, and I soon had it in as far and it would go. The feelings were indescribable. Joy, pride, fullness, euphoria, and a horniness that I have never felt before washed over me. There I was, laying on the bed, my own cock in one hand, dripping and weeping with joy, and my other hand holding and pushing that cock in my now stretched ass. Life just didn't get any better. Now, I don't know about most men, but I was raised with a healthy sense of guilt over anything sexual, and the thought creeped into my mind about whTat people, particularly my bitch of a wife would say if they walked in on me at that moment. There I was, legs spread and in the air, the hard-on from hell, and my ass stuffed with the most wonderful toy I had ever seen. Quickly, I dismissed that thought, and concentrated on that wonderful feeling. It was time to start the real fucking. I got a good hold on the suction cup at the base, and slowly began to pull it out. I heard a moan escape my lips, or was it a whimper? It doesn't matter, because it felt wonderful. After I got it about half-way out, I reversed directions and started pushing it back in. The great feelings started building again, and I slowly started fucking myself with that toy, building and building that wonderful feeling. Faster and faster I stroked my own cock and fucked my ass. I wasn't going to last long and didn't care. It felt too damn good to stop. Too quickly though, I erupted. I exploded. I came so hard I was dizzy and nearly passed out. When I finally came around, I had cum trailing from my nose to my belly button. Damn, I covered myself in cum, and I loved it. I wanted to ask myself if it was good for me! I wanted to roll over and have a smoke. I wanted to do it all over again. That explosion of pleasure was also the next step in my journey of sex with another man, or at least opened the door to it. I lay there, feeling better from sex than I had ever felt before, covered in my own cum, and breathing hard, opened my mouth to gulp some air, and a drop or two of my own cum fell into my mouth. Now, I had never tasted my own cum before...never even thought about it actually, but there I was, with a slight taste of my own cum in my mouth. In my post cum haze, I thought that it wasn't actually bad, and looked down to find a bigger taste. Scooping the cum from my belly to face, I looked at it, and quickly put it in my mouth before I lost my nerve. Not chocolate I thought, but not bad either. I didn't know it at the time, but I was now hooked on eating my own cum, like an addict looking for their next fix. Life went on that way for the next few months. I would get away by myself and play with my ass and eat my cum every chance I could get. Of course, it didn't take long to find my way back to the adult toy shop to find other toys to play with, and after about 6 months, I had quite a collection of toys to use on myself. Looking back on it, I realize that each trip to the store resulted in an ever increasing size of toys, and eventually ended up with toys that I no matter how much I wanted it or how hard I tried, I couldn't get in my hungry ass. Of course, I got to the point where I wanted to share this new found obsession with other, and I would get on line, log into AOL chat (this was when you could have a chat room about just about anything), and find a local gay chat room, figuring that would be where I would find like-minded men. I didn't really find many men that shared my same obsession, but I certainly found other men interested in using my ass for themselves. At first, I was a little turned off. I wasn't gay was I? I just liked playing with my ass and eating my own cum. But as time went, the longer I chatted with these men, the more curious I got. Of course, my health sense of guilt kicked in, and when I started really talking with them, I would get hot and horny over what they would tell me they wanted to do to me, all while sitting there with my ass plugged while talking to them, and then, after chatting, camming, and cumming, I would feel guilty about it, but I kept going back. Eventually the guilt because less, fading into the background, until I actually started considering giving it a try. There was one guy I chatted with fairly regularly, and he always hinted that if I ever wanted to give it a try, he would be more than happy to help me out. Sure, he wanted to help me out, but at the time, that is the only thing I chose to believe. Finally, after a couple months talking with him, letting him tease me and see me with my ass stuffed, and letting him watch me swallow my own cum like the greedy little whore I was becoming, I decided what the hell, it couldn't be any worse, it couldn't be any more gay than what I was already doing to myself, so I told him that we could meet and I would give him my ass cherry. You would think by his reaction that I had given him the best present in the world. Now in the time that we had been talking, I had never seen his face. He had sent me a couple cock shots, but wouldn't go on camera with me because he didn't want anyone to know who he was. He was an officer in the Air Force during the time of don't ask, don't tell, and didn't want to take any chances. I might mention that I was also in the Air Force (enlisted) at this time, and hadn't really thought of keeping my identity safe, so he knew what I looked like, but I didn't have a clue of who he really was. On the chosen Saturday, I gave myself a really good enema, and he gave me directions to his house and with more than a little fear, I made my way there. During the entire drive, I was terrified! What would it be like? What would he do to me? Would I like it? Would he like me? I damn near turned around and went back home! Finally, I made my way to his door and knocked. Answering the door, I had the big "aw fuck" moment when I realized I knew him! He was a pilot in a different squadron. I didn't know him personally, but I certainly had seen him before. He invited me in, and after the first couple awkward minutes, we started getting comfortable. After that, things began to move fast. Faster than I could have imagined. He looked at me, and said "I'm only going to ask this once. Are you sure you want this?" With a lot of fear in my voice, not even being able to look at him, I whispered "yes, more than anything." That is all it took. He moved quickly to me, taking my head and began kissing me, deep, hard and aggressively. Holy shit! I had never been the passive one when having sex, and now he had quickly and totally taken control of me. I started kissing him back, letting his tongue enter my mouth. He was taking, and I was giving. My cock, frightened beyond functioning before that point, began to respond, and respond fast. By the time he stopped kissing me, his hands were all over my body, and lost in lust, I wanted more. He looked at me, smiled a cocky, self-assured smile, and told me I was his bitch now. I damn near came right then! He stood up and took his sweat pants and t-shirt off quickly (he was prepared for me), and then sat back down on the couch. I couldn't stop staring at his rock hard cock. I had never thought about it before, but as I looked at his hard meat, all I could think was "god, it's beautiful." He let me look for a few seconds, and reached out to me again. I thought he was going to start kissing me more, but as he pulled me closer, he guided my head down, down towards that beautiful, hard, and ready cock. I didn't hesitate or resist. I went willingly. I opened my mouth as I got closer, and just like that, I was a cock sucker. Oh god it was wonderful. His cock filled my mouth in a way I had never dreamed before. He moved my head up and down on his meat a couple times until I got the idea of what he wanted and then started doing it on my own. Once I started, I went at that god-like cock like it was my last meal. Hitting the back of my mouth a couple times, I gagged, but was also determined to make this man happier than anyone had ever made him. Pushing forward, I swallowed a couple times until finally, gloriously, he slipped down my throat. I think I heard him moan, but can't be sure, I was too caught up in sucking my first cock, that everything around me faded into the distance, and the only thing I was aware of was that cock buried in my throat. I pulled up after a few seconds to get a breath, and went back to work on him. I wanted, no, I needed him to cum in my mouth. I needed to be the slut he had called me minutes before. Up and down I went, occasionally taking him back down my throat. I didn't want it to end, but he had other ideas, and he was in charge. Too soon for me, he grabbed hold of my head, and started fucking me like a doll, reminding me again that I wasn't in charge here, he was. His voice got louder and louder, and finally I heard him say, "here it comes slut. Swallow it, swallow it all my little slut," and then I felt the first shot of his cum in my mouth. One shot after another filled my mouth, and his cock was far enough in that I couldn't swallow, so I just let it fill my mouth. I was in heaven, and so was he apparently. Finally, letting go of my head, he looked down at me, smiled, and told me to swallow it. With a sheepish grin on my face that I couldn't control, I swallowed, then swallowed again until it was all in my belly. I felt like I had just won a gold medal I was so proud of myself. I could still taste his cum in my mouth, and all I could think was "you're a cock sucker now, and you will never go back." He pulled me up from my knees to him, and kissed me deeply and powerfully. I felt giddy. He whispered to me that I had done great, and that he now owned my mouth cherry. His words made me feel special and wonderful. I was a good cock sucker! Finally, after he recovered enough, he stood up, and helped me off the couch. Slowly, he undressed me, making me feel more naked than I have ever felt before. He looked me over, looked down at my rock hard cock and told me that I had a nice cock, but that we weren't there for my cock, we were there for his. He led me through the bedroom and into the bathroom, telling me that we were going to take a shower together. Getting into the shower together, we began to wash one another. It was sensual, sexy, and very intimate. Before we got out, he got his hands on my ass and began soaping and massaging me. My own cock hadn't gone down yet, but he ignored it and concentrated on my ass. It felt so good to have his hands on me. I melted back onto his hands, grinding my ass on his roaming hands. Finally, his finger found my puckered ass, and he slowly wormed first one, then two fingers up there. I moaned and wiggled, and then started begging for more. Chuckling at my greediness, he said "not my slut, I'm going to fuck your cherry ass, and your first time is supposed to hurt a little. I don't want to stretch it too much" Pulling his fingers out of my wanting ass, we got out of the shower and dried one another off, and he led me to the bedroom. I looked down at his cock, and noticed with a little pride that he had started to get hard again. I had made this man cum, and now I was making him hard again. He laid me down on the bed, and kneeled down beside me, his cock once again beside my head. He looked down, and told me to get him ready to take my ass. I damn near jumped on his cock again, hurrying to get his cock back in my mouth. Sucking, licking, and worshiping that cock, going after it like a man possessed. He immediately got hard, laughing at me and telling me that he had created the perfect slut, and told me to lay down on my back. I looked up at him as he reached over and grabbed the lube off the night stand. Looking back at me, he told me that he normally likes it doggy style, but this time, the first time, he wanted to look me in the face while he took my ass for the first time. Reaching down, he began to rub around the outside of my ass and get it slick. Soon, I felt his finger slide in me again, and I let out with another moan. Laughing at me, he pulled his fingers out again, and covered his perfect cock with lube and climbed on top of me. "OK slut" he said, "I am going to take you now, and before I'm done, you are going to know you were fucked." Pulling my legs up, he told me to hold my legs back so he could get at me. I held my legs to my chest, looking at him in what I hoped was a longing and wanting look, and told him to take me. I felt the bulb of his head against my ass, and was twitching in anticipation. I wanted this. I needed it. I don't know where it came from, and I certainly didn't mean to say it, but I heard myself in what was almost a whisper say "take me, please, take me." Grinning, he started slowly pushing into me. There was a little resistance at first, but finally, I felt the head of his cock pop in me. "Oh god yes" I said. Again, he was grinning down at me, knowing what he was doing to me. Then, without warning, without saying a word, he pushed hard. He pushed so hard his entire cock was shoved in my no longer virgin ass in one movement. Screaming before I could control it, I heard myself yell "fuck, it hurts." He just smiled at me, and as calm as could be, told me "I know that slut, the first time is supposed to hurt." I laid there, whimpering, my ass twitching around his invading cock. I was full! I was an ass slut. I had found myself. Slowly, the pain started going away, and it started to feel good. I sensed that I was ready, and began to gradually pull out. After hearing me moan no, he slammed back into me, getting a loud "oomph" from me. It didn't hurt as bad this time, and I reached around him, holding on to his ass to keep him from going anywhere (like that was going to happen), and pulled his beautiful cock in me as far as it would go. He slowly began to fuck me like I wanted and needed, sliding his cock almost all the way out before plunging in me again. Once again, I had found heaven. I was on cloud nine as he took me. His cock going in and out of me made me higher and higher with each thrust. After a few minutes, he was pounding me. He was using me again for his own pleasure, and I was his for the taking. I couldn't stop making noises. Grunting and moaning with each thrust, hearing my own voice telling him over and over to take me, to fuck me, to cum in me. This man, the man using me so completely, was sweating from the exertion of raping my ass. Glistening in sweat, he pumped harder and harder. After I don't know how long, minutes, an hour, all day, he looked down at me, and told me to start rubbing my rock hard cock. He told me not to cum until he told me to, but to be ready. By this point, it wasn't going to take much to make me cum, so I softly fondled and rubbed my own cock, aching with need to cum. He looked in my eyes again, saying get ready slut, I'm almost there. Whispering and grunting with every stroke of his, I told him I was ready. Finally, she howled, screamed and told me to cum. As we both exploded, him filling my ass with his seed, and mine exploding between us, I heard him yell with each of his explosive thrust...you (slam) are (slam) my (slam) slut (slam) now (slam)! Fulfilled, filled and satisfied beyond belief, happier than I have ever been before, I looked into his eyes, and the only thing I could say, the only thing that made sense, what came out of my mouth automatically without thought, was "yes sir, I am."